59345-33-4

Upstream product

• 529-28-2 4-iodoanisol 
• 10486-08-5 sodium p-thiocresolate 
• 103-19-5 di(p-tolyl) disulfide 
• 100-66-3 methoxybenzene 
• 53271-41-3 S-(p-tolyl) 2-methoxybenzothioate 
• 624-31-7 4-tolyl iodide 
• 7217-59-6 2-Methoxybenzenethiol 
• 106-45-6 para-thiocresol 
• 578-57-4 2-bromoanisole 
• 492-95-5 2-methoxyphenyldiazonium tetrafluoroborate 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 5720-06-9 2-Methoxyphenylboronic acid 
• 38078-55-6 sodium S-(4-methylphenyl) thiosulfate 
• 934-72-5 Methyl p-tolyl sulfoxide 

Downstream Products

• 10371-01-4 2-[(4-methylphenyl)sulfonyl]phenol 
• 320576-23-6 o-methoxyphenyl p-tolyl sulfoxide 

Relevant academic research and scientific papers

Paired Electrolysis Enabled Ni-Catalyzed Unconventional Cascade Reductive Thiolation Using Sulfinates

Herein, we have reported a nickel-catalyzed cascade reductive thiolation of aryl halides with sulfinates driven by paired electrolysis. This protocol uses sulfinates as the sulfur source, and various thioethers could be synthesized under mild conditions. By mechanism exploration, we find that a cascade chemical step is allowed on the electrode interface and could alter the reaction pathway in paired electrolysis, whose findings could help the discovery of novel cascade reactions with unique reactivity.

Dechalcogenization of Aryl Dichalcogenides to Synthesize Aryl Chalcogenides via Copper Catalysis

An application for dechalcogenization of aryl dichalcogenides via copper catalysis to synthesize aryl chalcogenides is disclosed. This approach is highlighted by the practical conditions, broad substrate scope, and good functional group tolerance with several sensitive groups such as aldehyde, ketone, ester, amide, cyanide, alkene, nitro, and methylsulfonyl. Furthermore, the robustness of this methodology is depicted by the late-stage modification of estrone and synthesis of vortioxetine. Remarkably, synthesis of more challenging organic materials with large ring tension under milder conditions and synthesis of some halogen contained diaryl sulfides which could not be synthesized using metal-catalyzed coupling reactions of aryl halogen are successfully accomplished with this protocol.

Palladium-Catalyzed Enantioselective C?H Olefination of Diaryl Sulfoxides through Parallel Kinetic Resolution and Desymmetrization

The first example of PdII-catalyzed enantioselective C?H olefination with non-chiral or racemic sulfoxides as directing groups was developed. A variety of chiral diaryl sulfoxides were synthesized with high enantioselectivity (up to 99 %) throu

Thieme Chemistry Journals Awardees - Where Are They Now?Molybdenum(V)-Mediated Synthesis of Nonsymmetric Diaryl and Aryl Alkyl Chalcogenides

Oxidative chalcogenation reaction using molybdenum(V) reagents provides fast access to a wide range of nonsymmetric aryl sulfides and selenides. The established protocol is tolerated by a variety of labile functions, protecting groups, and aromatic heterocycles. In particular, when labile moieties are present, the use of molybdenum(V) reagents provides superior yields compared to other oxidants.

Ni nanoparticles on RGO as reusable heterogeneous catalyst: Effect of Ni particle size and intermediate composite structures in C-S cross-coupling reaction

The present work demonstrates the C-S cross-coupling reaction between aryl halides and thiols using nickel nanoparticles (Ni NPs) supported on reduced graphene oxide (Ni/RGO) as a heterogeneous catalyst. It is observed that the uniformly dispersed Ni NPs supported on RGO could exhibit excellent catalytic activity in C-S cross-coupling reactions and the catalytic application is generalized with diverse coupling partners. Although the electron-rich planar RGO surface helps in stabilizing the agglomeration-free Ni NPs, the catalytic process is found to occur involving Ni(II) species and the recovered catalyst containing both Ni(0)/Ni(II) species is equally efficient in recycle runs. A correlation of loading of Ni species, size of NPs and the intermediate Ni-related heterostructures formed during the catalytic process has been established for the first time, and found to be best in the C-S cross-coupling reaction for Ni(0) and Ni(II) NPs of the average sizes 11-12 nm and 4 nm, respectively.

Visible-light-promoted synthesis of diaryl sulfides under air

A convergent, organocatalytic visible-light-mediated process for the synthesis of diaryl sulfides has been developed. A broad range of aryl thiols reacted with various aryl diazonium salts in the presence of eosin Y under air atmosphere to afford the desired diaryl sulfides in high yields. This novel and environmentally friendly method provides an alternative route to established synthetic approaches.

An aryl thioether synthetic method of the compound

The invention discloses a synthetic method of an aryl sulfide type compound shown by a formula (3). In a reaction solvent, an aryl or alkenyl thiosulfate type derivative and a boric acid, boric acid grease or borate type derivative are used as reaction raw materials and react with each other to obtain a polysubstituted aryl sulfide type compound under the action of a metal copper catalyst. According to the synthetic method disclosed by the invention, reaction conditions are mild, raw materials are easily-available and low in price, the reaction operation is simple, the yield is relatively high, and a key skeleton structure is provided for the synthesis of many natural products and medicaments, so that the method can be widely applicable to industrial scale production. A formula is shown in the specification.

Tridentate hydroxy-functionalised MCM-41-immobilised copper(I) complex as an efficient and recyclable catalyst for coupling of aryl iodides with thiols

The C-S coupling reaction of aryl iodides with thiols was achieved at 110 °C in DMF/dioxane (V/V, 1:9) in the presence of a tridentate hydroxy-functionalised MCM-41-immobilised copper(I) complex [MCM-41-3OH-CuI] with Cs2CO3 as base to afford a variety of diaryl sulfides in good to excellent yields. The MCM-41-3OH-CuI catalyst can be easily recovered by a simple filtration and reused for at least six times without significant loss of activity.

CO2-promoted oxidative cross-coupling reaction for C-S bond formation via masked strategy in an odourless way

Cu-catalyzed direct oxidative cross-coupling between boronic acids and masked sulfides delivering thioethers was described, in which the SO3-, as a mask, has shown a distinctive effect on the oxidative cross-coupling condition. Disulfide could be suppressed efficiently via masked strategy under CO2 atmosphere. A broad scope of aromatics and scalable processes indicates its practicality, which could be further applied to drug late-stage modification and unsymmetrical dibenzothiophenes (DBTs) synthesis.

Reaction of arynes with sulfoxides

A S-O bond insertion reaction of sulfoxides with arynes is reported. This reaction represents a rare instance of semipolar single bond insertion in aryne chemistry. The study of mechanism indicates that a sulfur ylide triggered by aryne is the key intermediate, which further transfers its methylene group to carbonyl compounds to give epoxides and thioethers through a sequential process.